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Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building.
Make memories the whole family will cherish in this great family...
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***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***
MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS
Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light...
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You have use of one of four private cabins with a private marine style bathroom. Three cabins available for rent. You will share the common areas with new friends. The cabin is air conditioned with a queen like bed. Captain Charles and wife Deborah use one cabin. When conditions allow we offer a...
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This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic...
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Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West...
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TAKE 20% OFF:
-- Stay September 3-6 (3 nights) and pay a reduced rate of $850 for all three nights instead of $1,065.
-- Note, taxes and fees will be added to all rates....
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FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after...
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Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends.
Experience endless sunshine and the incomparable...
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Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the...
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Live in luxury poolside in a beautifully furnished studio (private room and full bath) apartment, situated in a quiet, coveted residential Key West neighborhood. Walk right outside your door into an enchanting, very nicely landscaped pool/deck area for your enjoyment. You'll be strategically...
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The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping....
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You have the use of one of four private cabins each with its own marine style bathroom and queen like bed for $235.. Three cabins available for six or less guest for $695. Captain Charles and wife Deborah use one cabin. You may choose our sunset sail for $50 per person that includes snacks and non...
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Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and...
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This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.
This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the...
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Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine...
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Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town...
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Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in...
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All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2...
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Quiet, quaint and conveniently located in the heart of key west. This small little condo is a great place to rest your head after a day on the beach, out on a boat or after enjoying a stroll down Duval street. It is located on a quiet street in Bahama village. The beach is 10 blocks away. Duval...
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What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy.
Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet....
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BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :)
As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with
Beach ,...
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******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a...
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For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of...
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SUNSET CELEBRATION: Coming Soon!2 bedroom 1 bath Shipyard condo located in Truman Annex. Currently undergoing renovation to include new floors, fresh paint, all new furnishings, artwork, linens and towels. Be the first to stay in this totally updated vacation home.Master bedroom will have queen bed...
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Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your...
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Two bedroom, two bath, totally renovated in 2015, all new, marble floors, 10 foot ceilings, granite counters, walking distance to all major tourist attractions, one site parking, one block from Southernmost Point, one block from famous Duval Street. local beach is less than one mile, restaurants,...
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We are situated in New Town on the paradise island of Key West, about 12 minutes drive from downtown Duval Street.
This romantic studio cottage consists of a bedroom with very comfortable king sized bed and a bathroom, with a pool and lush landscaping right outside your door. It has air...
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2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6).
Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered...
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Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It...
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WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine with ocean breezes wafting by. Condo offers street view; complex offers...
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The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse...
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28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon...
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Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at...
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BEACH HOUSE CONDO: 2 bedroom 2 bath downstairs condo in the gated Shipyard Condominium area of Truman Annex. The perfect back deck to sip a cafe con leche or grill your fresh catch. Open floor plan with kitchen, dining area for 4 and living room that opens to a large private deck. The master...
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Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,...
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This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning...
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Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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OSPREY: Studio cottage located in The Colony Suites, a compound nestled in Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room. Sunny and bright, sitting area, queen size bed, full bathroom and kitchenette. French doors open to a private...
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Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

Where To Rent a Vacation Home in Key West

Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Many House Rentals Near Attractions and Activities For All Ages

Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

Key West Bars and Restaurants

Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Book a Key West Vacation Rental For Your Next Trip

Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.

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